Concentrated sabadilla extract

ABSTRACT

The invention relates to methods for preparing a concentrated sabadilla extract and to methods of its use as a pesticide.

FIELD OF THE INVENTION

The present invention is directed to methods of preparing a concentratedsabadilla extract and methods of its use as a pesticide.

BACKGROUND OF THE INVENTION

Controlling damaging pests on plants grown to provide human food is aconstant struggle for growers. Insects can completely destroy a harvestand can cause catastrophic food shortages or financial ruin for thegrowers. Although many products are effective against insects thatdamage plants, the products must also be safe enough to be released intothe growing environment and safe enough to be applied to parts of theplants that will eventually be consumed.

Organic farming is increasing in popularity. Organic farming restrictsthe use of compounds that are used for pest control to encouragesustainability and safety. Pesticides can be used in organic farming ifthey are considered “natural.” Unfortunately, many of the naturalinsecticides currently available are not potent enough to provideadequate insect control. Further, many of the currently availablenatural pesticides are not practical to apply or their application iscost prohibitive.

One effective naturally derived insecticide is found in the tissues ofmany of the plants of the genus Schoenocaulon, commonly referred to assabadilla. The species with the longest history of use, and the mostreadily available, is Schoenocaulon officinale. The plant is indigenousto Central and South America and its seeds have been used for centuriesfor their insecticidal properties. The seeds contain the alkaloidsveratridine and cevadine, both of which are known to be active againstarthropods.

Usually the dried seeds are ground to a powder and the powder is applieddry or wetted to the insects or their environment. The seeds must bemilled into smaller particles in order to be applied to the insects. Themilling process usually requires an oil absorbing adjuvant to preventthe seeds from caking. This adjuvant dilutes the alkaloids in the groundseeds. Also, the ground seeds can be difficult to apply to areas in needof treatment because the seeds' particles and anti-caking adjuvant canclog spraying equipment. Another disadvantage of using ground seeds isthat the dust from the seeds can cause eye and nasal irritation.Further, the ground seed powder is often not potent enough to controllarge infestations.

U.S. Pat. Nos. 2,348,949 and 2,390,911 disclose the use of groundsabadilla seeds with beta-butoxy-beta-prime-thiocyanodiethyl-ether tocontrol houseflies. Further, these patents teach heating the seeds andusing them as a powder, or mixing them with kerosene to form a sprayableformulation. Neither of these disclosed mixtures of ground sabadillaseeds would be appropriate for organic farming.

Accordingly, there is a need for new methods of controlling insects. Themethods should be potent, safe for growers to apply, safe to beneficialorganisms (target specific), and safe for the environment.

SUMMARY OF THE INVENTION

In one aspect, the present invention is directed to methods forpreparing sabadilla extract.

In another aspect, the present invention is directed to methods forcontrolling pests comprising applying sabadilla extract to pests or totheir environment.

In a further aspect, the present invention is directed to a concentratedpesticidal sabadilla extract product produced by the process comprisingthe steps of milling sabadilla seeds or other plant parts, washing themilled sabadilla seeds or other plant parts with at least one seed andplant part solvent selected from the group consisting of methanol,ethanol, glycol ether, ethyl lactate, propanol, butyl lactate,gamma-butyrolactone, and 1-butanol under agitation to produce a solutionof sabadilla extract in the seed and plant part solvent, removing thesolution from the washed milled seeds, and removing the seed and plantpart solvent from the solution to produce the sabadilla extract.

In a preferred embodiment, the sabadilla extract is prepared fromSabadilla seeds.

DETAILED DESCRIPTION OF THE INVENTION

Applicant has unexpectedly developed new methods of producing aconcentrated sabadilla extract. Applicant was able to develop a methodto remove the solid inert seed parts, such as the cellulose,hemicellulose, lignin and pectin, from the rest of the seed componentswith methanol. This method produces an extract that contains thealkaloids in a more concentrated form. This method generally involvesusing a solvent to separate the solid inert seed or other plant partsfrom the resin, oil, and active compounds in the seed or plant. Theresin, oil and active compounds are dissolved in the solvent, such asmethanol, during agitation with milled seeds or other plant parts. Theconcentrated sabadilla extract remains when the solvent and washedmilled seeds or plant parts are removed.

The concentrated sabadilla extract is more effective than ground wholeseeds or plant parts because the inert parts of the seeds or plant partshave been removed. Further, the inert parts of the seeds or plant partscan no longer clog spray equipment. Yet another advantage of theconcentrated sabadilla extract is that it is easier to handle and can beformulated in various user-friendly products to meet the needs ofgrowers. Applicant's methods for production of the concentratedsabadilla extract are also high yielding and can be easily scaled up forcommercial use.

In one embodiment, the present invention is directed to methods forproducing concentrated insecticidal sabadilla extract comprising millingsabadilla seeds or other plant parts, washing the milled sabadilla seedsor other plant parts with at least one seed and plant part solventselected from the group consisting of methanol, ethanol, glycol ether,ethyl lactate, propanol, butyl lactate, gamma-butyrolactone, and1-butanol under agitation to produce a solution of sabadilla extract inthe seed and plant part solvent, removing the solution from the washedmilled seeds or other plant parts, and removing the seed and plant partsolvent from the solution to produce the sabadilla extract.

Sabadilla seeds and extract may be derived from any species ofSchoenocaulon. The genus Schoenocaulon includes the following species:Schoenocaulon calcicola, Schoenocaulon caricifolium, Schoenocauloncomatum, Schoenocaulon conzattii, Schoenocaulon dubium (alt.Schoenocaulon gracile), Schoenocaulon framei, Schoenocaulonghiesbreghtii (alt. Schoenocaulon drummondii, Schoenocaulonyucatanense), Schoenocaulon ignigenum, Schoenocaulon intermedium,Schoenocaulon jaliscense, Schoenocaulon macrocarpum (alt. Schoenocaulonlauricola), Schoenocaulon madidorum, Schoenocaulon megarrhizum,Schoenocaulon mortonii, Schoenocaulon oaxacense, Schoenocaulon obtusum,Schoenocaulon officinale, Schoenocaulon pellucidum, Schoenocaulonplumosum, Schoenocaulon pringlei, Schoenocaulon rzedowskii,Schoenocaulon tenorioi, Schoenocaulon tenue, Schoenocaulon tenuifolium,Schoenocaulon texanum, and Schoenocaulon tigrense.

In a preferred embodiment, the sabadilla seeds can be derived from S.officinale.

To optimize solvent penetration and subsequent extraction, the seed coatmust be ruptured and the distance between penetrable surfaces of theseed reduced as much as possible. The can be achieved by milling theseeds.

Sabadilla seeds are very difficult to cleanly break into fine pieces.The bulk of the seed is hard and oily and requires a lot of energy topulverize, producing heat due to high friction. Any suitable millingmethod can be used. Applicant found that cryogenic hammer milling theseeds was ideal for efficient extraction of the sabadilla oil.

Cryogenic grinding, or cryomilling, most commonly uses dry ice, liquidcarbon dioxide or liquid nitrogen to cool the feed material in a mill ofan otherwise conventional design (e.g. a cryogenic hammermill.) Thissuper-cooling makes the sabadilla seed more uniformly brittle, in turnmaking it easier to control particle size. Additionally, the oil in theseed is a solid at the temperature of liquid nitrogen, and does not slowprocessing speed. This increased friability and solidification of theoil allows for very efficient throughput rates during milling.

Flake milling, most commonly using a roller-type mill, was found tocreate a milled sabadilla seed that was somewhat more efficient tohandle during processing than cryogenically hammer milled seed, butallowed a less efficient extraction. In a flake milling procedure, theseeds are heated to increase plasticity and passed between rollers whichflatten the seeds into thin, solvent-penetrable flakes that are stilllargely one piece. Flaking usually produces a minimal amount of fineparticles which hinder efficient processing.

Pin milling may also be used but this technique produces particles whichare coarse and require more time to process than other milling products.Conventional, ambient, hammer milling and “Fitz” milling may also beused to produce a sufficiently sized particle, however, throughput ratesare generally inefficient and it is difficult to control particle size.

While flake milling's larger particle size overall makes it simplest andeasiest to handle during processing, Applicant found that cryogenichammer milling allowed the creation of sabadilla seed particles over arange of sizes that enable a more efficient extraction of sabadilla oilwith only a modest increase in material handling difficulty.Accordingly, Applicant found that cryogenic hammer milling with liquidnitrogen was a superior milling approach for producing sabadilla oil.

The milled sabadilla seeds can be washed with the seed and plant partsolvent one time or multiple times. For example, the milled sabadillaseeds can be washed one to ten times. If the seed and plant part solventis decanted and additional solvent added (additional washes), then theyield is increased.

In an embodiment, the milled sabadilla seeds are washed the seed andplant part solvent from 1 to 5 times. In a preferred embodiment, themilled sabadilla seeds are washed with the seed and plant part solventfrom 2 to 5 times. In a most preferred embodiment, the milled sabadillaseeds are washed with the seed and plant part solvent 5 times.

The sabadilla extract can be washed with the extract solvent one time ormultiple times. For example, the sabadilla extract can be washed one toten times.

In an embodiment, the seed or plant part solvent solution is removedfrom the washed milled seeds by decanting (pouring), pumping, ordraining. For example, when the extract is produced on a small scale,the milled seeds settle to the bottom of the flask and the seed or plantpart solvent solution can be easily decanted out of the flask. Duringcommercial extraction production, the seed or plant part solventsolution can be removed by methods known by those of skill in the art.For example, the seed and plant part solution could be removed from thewashing vessel by draining the methanol with the use of a screen, pump,or filter.

In another embodiment, sabadilla oil can be extracted from milledsabadilla seeds using countercurrent extraction. Countercurrentextraction is a commercial scale extraction process typically used inoil seed extraction of seeds such as canola and soy. In brief,countercurrent extraction is a continuous process in which fresh, milledseed is fed through a long solvent bath by conveyor. The seed enters oneend and the solvent enters the other, both eventually exiting oppositeends of the apparatus as spent marc (i.e. extracted/depleted seed) andmiscella (i.e. solvent with a solute load from the seed).

During the extraction, the milled sabadilla seeds and seed or plant partsolvent should be agitated. This can be done by any method known bythose of skill in the art. Applicant found that stirring the milledsabadilla seeds in the solvent increased the rate of extraction and wasan effective means of agitation. The process was most efficient if thestirring was brisk enough to prevent the milled sabadilla seeds fromsettling in the extraction/washing vessel (e.g., flask).

During the extraction, the sabadilla extract and extract solvent shouldbe agitated. This can be done by any method known by those of skill inthe art. The process was most efficient if the stirring was brisk enoughto prevent the sediment from the sabadilla extract from settling in theextraction/washing vessel (e.g., flask).

In a preferred embodiment, the seed and plant part solvent is selectedfrom the group consisting of methanol, ethanol, glycol ether, ethyllactate, and propanol. In a more preferred embodiment, the seed or plantpart solvent is methanol.

Methanol can be used at temperatures from about 0 to about 60 degreesCelsius. Applicant found that methanol at lower temperatures requiredadditional extraction time and that temperatures above about 55 to about60 degrees Celsius resulted in methanol loss and boiling. Applicantfound that the optimal temperature for methanol extraction was fromabout 50 to about 55 degrees Celsius.

In an embodiment, the methanol is removed from the sabadilla extract andsolvent solution by evaporation, including distillation.

In another embodiment, the present invention is directed to methods forcontrolling pests comprising applying the concentrated sabadilla seedextract produced by the methods of the present invention to pests or thepests' environment.

In another embodiment, the pests controlled are selected from the groupconsisting of members of the class Insecta (insects), Arachnida subclassAcari (mites), and shell-less terrestrial gastropod mollusks (slugs).

In an embodiment, the insects controlled are selected from the groupconsisting of aphids (Hemiptera), whiteflies (Hemiptera), thrips(Thysanoptera), leafhoppers (Hemiptera), bed bugs (Hemiptera), psyllids(Hemiptera), scale insects (Hemiptera), mealybugs (Hemiptera), psocids(Psocoptera), lice (Phthiraptera), fleas (Siphonaptera), caterpillars(Lepidoptera), and early immature stages of beetles (Coleoptera), truebugs (Hemiptera), cockroaches (Blattodea), flies (Diptera) and wasps(Hymenoptera). In a preferred embodiment, the insects controlled areselected from the group consisting of aphids (Hemiptera), whiteflies(Hemiptera), thrips (Thysanoptera), leafhoppers (Hemiptera), bed bugs(Hemiptera), psyllids (Hemiptera), scale insects (Hemiptera), mealybugs(Hemiptera), psocids (Psocoptera), lice (Phthiraptera), and fleas(Siphonaptera). In a more preferred embodiment, the insects controlledare selected from the group consisting of bed bugs (Cimex lectularius),western flower thrips (Frankliniella occidentalis), green peach aphids(Myzus persicae), and greenhouse whitefly (Trialeurodes vaporariorum).

In a preferred embodiment, the mites controlled are two-spotted spidermites (Tetranychus urticae).

The sabadilla extract is a contact pesticide which means that theextract should be applied directly to the pests or their environment forthe most effective control. The extract, or a formulation containing theextract, can be mixed with water and applied with a pressurized system,such as aerosol generators or in a form of ground application, e.g., lowpressure boom sprayers, high pressure sprayers, air blast sprayers, lowvolume air sprayers (mist blowers), hand-operated sprayers and pumpsprays. The extract should be applied as a fine spray until the surfaceis uniformly wet with minimal runoff. In another embodiment, the extractcan be formulated, for example, as granules, and applied by broadcast.

In a further embodiment, the present invention is directed to aconcentrated insecticidal sabadilla extract product produced by theprocess comprising the steps of milling sabadilla seeds, washing themilled sabadilla seeds with at least one seed and plant part solventselected from the group consisting of methanol, ethanol, glycol ether,ethyl lactate, propanol, butyl lactate, gamma-butyrolactone, and1-butanol under agitation to produce a sabadilla extract seed and plantpart solvent solution, removing the solution from the washed milledseeds, and removing the seed and plant part solvent from the solution toproduce the pesticidal sabadilla extract. In a preferred embodiment, thesabadilla seeds can be derived from the S. officinale.

As used herein, “concentrated sabadilla extract” refers to an extract ofsabadilla seeds or other plant parts which is substantially free ofcellulose, hemicellulose, lignin, and pectin.

The concentrated sabadilla extract of the present invention is distinctfrom sabadilla seeds in their natural state because the extract has beenisolated from the seed and concentrated. The sabadilla extract of thepresent invention is not present in nature in this form.

As used herein, “controlling pests” refers to decreasing the negativeimpact of pests on plants or animals to a level that is desirable to thegrower or animal.

As used herein, “roller mill” refers to equipment used to decrease theshape of a material by pressing the material with at least onecylindrical roller against another roller or firm surface. A roller millis one way of producing a flaked seed.

As used herein, “pests' environment” refers to any area that the pest ispresent during any life stage. One environment likely to be treated bythe methods of the present invention includes the plants that the pestsare living on and the surrounding soil. The pests' environment mayinclude soil, plants, harvested plants, gardens, fields, greenhouses, orother buildings, and various indoor surfaces and structures, such asfurniture including beds, and furnishings including books, clothing,etc.

As used herein, all numerical values relating to amounts, weightpercentages and the like are defined as “about” or “approximately” eachparticular value, namely, plus or minus 10% (±10%). For example, thephrase “at least 5% by weight” is to be understood as “at least 4.5% to5.5% by weight.” Therefore, amounts within 10% of the claimed values areencompassed by the scope of the claims.

The articles “a,” “an” and “the” are intended to include the plural aswell as the singular, unless the context clearly indicates otherwise.For example, the methods of the present invention are directed tocontrolling “pests” but this can include control of a single pest (suchas a single insect).

The following examples are intended to illustrate the present inventionand to teach one of ordinary skill in the art how to use the extracts ofthe invention. They are not intended to be limiting in any way.

EXAMPLES Example 1

Sabadilla seeds were flake milled according to the manufacturer'sinstructions. Two hundred grams of milled seed were added to a threeliter flask with methanol and stirred with a three blade stirrercontrolled by an overhead motor. A stirring speed was maintained whichprevented any seed fragments from settling in the flask. The system wassealed to limit evaporation loss.

The methanol was decanted off and additional methanol was added to theflask. This step was repeated three additional times.

The sabadilla extract containing methanol solution was then placed in anew flask. Distillation was used to remove the methanol from thesabadilla extract containing methanol solution. Standard IKA rotaryevaporators were used for the distillation. The flask containing thesabadilla extract containing methanol solution was loaded into theevaporator and into a heated water bath. The flask was heated to between50 to 55 degrees Celsius in order to maximize efficient removal of themethanol without allowing it to boil over into the condenser. Theevaporated methanol was thoroughly condensed in an adjoining flaskleaving the solute/extract.

Accordingly, a concentrated sabadilla extract was prepared.

We claim:
 1. A method for producing a concentrated pesticidal sabadillaextract comprising: milling sabadilla seeds or other plant parts with aroller mill; washing the milled sabadilla seeds or other plant partswith at least one seed and plant part solvent selected from the groupconsisting of methanol, ethanol, glycol ether, ethyl lactate, propanol,butyl lactate, gamma-butyrolactone, and 1-butanol under agitation toproduce a sabadilla extract containing seed and plant part solventsolution; removing the sabadilla extract containing seed and plant partsolvent solution from the washed milled seeds or other plant parts; andremoving the seed and plant part solvent from the solution to producethe concentrated sabadilla extract.
 2. The method of claim 1 wherein thesabadilla seeds are sabadilla officinale seeds.
 3. The method of claim 1wherein the milled sabadilla seeds are washed with the seed and plantpart solvent from 2 to 5 times.
 4. The method of claim 1 wherein themilled sabadilla seeds are agitated in the seed and plant part solventby stirring.
 5. The method of claim 1 wherein the seed and plant partsolvent is methanol.
 6. A method for controlling pests comprisingapplying the concentrated sabadilla extract produced by the method ofclaim 1 to pests or the pests' environment.
 7. The method of claim 6wherein the pests are selected from the group consisting of members ofthe class Insecta, Arachnida subclass Acari, and shell-less terrestrialgastropod mollusks.
 8. The method of claim 6 wherein the pests areinsects.
 9. The method of claim 8 wherein the insects controlled areselected from the group consisting of aphids (Hemiptera), whiteflies(Hemiptera), thrips (Thysanoptera), leafhoppers (Hemiptera), bed bugs(Hemiptera), psyllids (Hemiptera), scale insects (Hemiptera), mealybugs(Hemiptera), psocids (Psocoptera), lice (Phthiraptera), fleas(Siphonaptera), caterpillars (Lepidoptera), beetles (Coleoptera), truebugs (Hemiptera), cockroaches (Blattodea), flies (Diptera) and wasps(Hymenoptera).
 10. A concentrated insecticidal sabadilla extract productproduced by the process comprising the steps of: milling sabadilla seedsor other plant parts; washing the milled sabadilla seeds or other plantparts with at least one seed and plant part solvent selected from thegroup consisting of methanol, ethanol, glycol ether, ethyl lactate,propanol, butyl lactate, gamma-butyrolactone, and 1-butanol underagitation to produce a sabadilla extract containing seed and plant partsolvent solution; removing the solution from the washed milled seeds orother plant parts; and removing the seed and plant part solvent from thesolution to produce the concentrated sabadilla extract.
 11. The productof claim 10 wherein the sabadilla seeds are Schoenocaulon officinaleseeds.